Triethylamine → HCID 13509355, compound

HRID 235624Notes

Reaction equation

HRID 235624 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])=[N:8][CH:9]([CH3:13])[NH:10][C:11]=1[CH3:12])=[O:5])[CH3:2].C(N(CC)CC)C.[CH2:30]([O:32][C:33](Cl)=[O:34])[CH3:31].C(Cl)(Cl)Cl>>[CH3:13][C:9]1[N:8]([C:33]([O:32][CH2:30][CH3:31])=[O:34])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:11]([CH3:12])[N:10]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 20191108HCID 20191108, compoundHCID 86741258HCID 86741258, compound

Product 1

HCID 13509355HCID 13509355, compound

Procedure

To a solution of 5-ethoxycarbonyl-2,6-dimethyl-4-(2'-nitrophenyl)-dihydropyrimidine (756 mg, 2.49 millimole) and triethylamine (374 mg, 3.7 millimole) in 30 ml of chloroform ethyl chlorocarbonate (406 mg, 3.74 millimole) was added dropwise with stirring in ice and the mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with 2% aqueous NaOH solution and water, dried and evaporated to remove the solvent. The obtained oil (730 mg) was purified on silica gel by column chromatography and eluted with 1% MeOH/CHCl3 to obtain the title product as crystals. The crystals were recrystallized from acetone-n-hexane to obtain colorless prisms (m.p. 130°-131.5°, 290 mg, 31% yield).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. washThe reaction mixture was washed with 2% aqueous NaOH solution and water
  3. customdried
  4. customevaporated
  5. customto remove the solvent
  6. customThe obtained oil (730 mg) was purified on silica gel by column chromatography
  7. washeluted with 1% MeOH/CHCl3

Sources & evidence

ORD record
ord-e2b6ee25c6e7489db590107188b3438d
Source dataset
uspto-grants-1987_02
Patent number
US04640922

Reaction notes

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